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experience

Indoor Pickleball + Bar at Pickle & Pint image 1

Two hands clinking a glass of red wine and a pint of beer over a wooden table beside a pickleball paddle and yellow pickleball in an indoor court — casual cheers scene.

Indoor pickleball facility with multiple blue-and-green courts under steel beams, players warming up and rallying across nets beneath bright overhead lights.

Two hands clinking drinks — a to-go iced coffee in a plastic cup and a glass of red wine against a green-and-white striped wall.

Two women in green shirts take a selfie on a brown leather couch in a pickleball-themed café, holding an iced coffee, a paddle and a neon-yellow pickleball against a green-and-white striped wall.

Two players on an indoor pickleball court, crouched and ready to return a shot—woman in a visor and skirt and partner in a red sleeveless top holding paddles on a blue-green court with the ball in play.

Indoor Pickleball + Bar at Pickle & Pint image 7

Assorted crackers and multigrain crisps with several orange cheese balls and two herbed cream-cheese spreads on a white rectangular platter with wooden-handled spreaders, set on a wooden patio table.

Top-down: pepperoni pizza and a toasted sandwich with potato chips on white square plates over a rustic wooden table.

Action shot of a player on an indoor pickleball court holding a paddle as a bright yellow perforated pickleball hovers above it

Three women in sporty outfits walk along a sunny concrete parking lot past a white corrugated storefront with bold green lettering, one carrying a checkered pickleball paddle.

Two women in sporty outfits laugh on a brown leather couch holding pickleball paddles in an indoor pickleball lounge with a mint-green striped mural showing pickleball and pint icons.

Casual patrons seated along a long wooden bar in an industrial-style brewery taproom, watching sports on three wall-mounted TVs above high stools and a concrete floor.

Patrons seated at a wooden bar inside an indoor pickleball sports venue, man in a white cap wearing a 'Pickle & Pint' shirt with paddle, ball and bottle graphic, TV screens showing sports on the wall.

Hand with white nail polish and colorful bracelets holding an iced coffee in a clear plastic cup with green straw against a blurred indoor sports court and bokeh overhead lights.

Two pint glasses of pale and amber beer clinking inside an indoor pickleball facility, with blue courts and blurred players in the background

Post-game cheers: two players clink beer glasses beside an indoor pickleball court, smiling with blue courts, nets, and a sports facility interior in the background.

Two players clinking pickleball paddles over an indoor blue pickleball court and net

Player in a white cap prepares to serve on bright blue indoor pickleball courts with multiple nets, other players and a high warehouse-style ceiling

Stacked pickleball paddles on a court-side fence at an indoor pickleball facility with players rallying on blue courts under bright ceiling lights.

Cheesy pepperoni pizza on a round metal tray atop a wooden bar counter with a frothy pint of craft beer blurred in the background — casual pizzeria scene

Two pickleball paddles with patterned faces and black grips beside a bright yellow pickleball on a blue court near a white diagonal line separating a teal area, playful ready-for-game composition.

Cafe-style toasted turkey sandwich halves with fresh greens and crunchy crinkle-cut potato chips on a white plate atop a wooden table

Iced coffee with green straw and a chilled water glass on coasters on a wooden café table, toasted sandwich and pizza slice blurred in the foreground — casual brunch scene.

Indoor Pickleball + Bar at Pickle & Pint

2hr

From $40/party

experience

Cheerful group of women in colorful dresses toasting with champagne flutes and mimosas at an indoor celebration

Vibrant brunch spread on a kitchen island featuring a tiered fruit and macaron tower with grapefruit halves, green grapes and red grapes, charcuterie and cheese cubes, green wellness shots and strawberry‑garnished orange mimosas, plus a bright floral centerpiece in the background.

Indoor home brunch buffet with a colorful floral centerpiece and tiered display of avocado crostini, wraps, pastries, skewers and cheese cubes.

Vibrant floral centerpiece on a granite home kitchen island hosting a brunch buffet: sliders, pastries, skewered bites, mini tarts, fresh fruit, and wicker bar stools.

Women in pink satin robes and sleep masks celebrating a bachelorette party behind shimmering purple streamers in a narrow indoor hallway, one holding a champagne bottle

Indoor mimosa bar in a modern kitchen: marble-topped brunch cart with carafes of orange and berry juice, hanging champagne flutes, floral garland and 'cheers' sign, chilled champagne bottles, stainless steel fridge and green chevron backsplash.

Brunch grazing board on a wooden dining table: three-tiered stand of muffins and mini pastries, plates of breakfast sliders, mini pancake shots with syrup droppers, yogurt berry cups, fresh fruit platter, cookies and citrus halves, surrounded by eucalyptus garland for a bright indoor birthday brunch setup.

Bridal party: four women in satin robes (bride in white, bridesmaids in pink) lying upside down on a bed toasting mimosas in a cozy bedroom getting-ready scene.

Mimosa bar setup in a modern kitchen: marble-top cart with carafes of orange and berry juices, hanging glasses, floral garland and 'cheers' sign, champagne bottles on ice beside a decorated table, grey cabinets and stainless fridge with green herringbone backsplash.

Indoor party setup: white champagne cart decked with pink and orange balloons and glassware beside a white-clothed dessert table with tiered platters of pastries, fruit, flowers and gold accents against a white brick wall on a wood floor.

Four white plates on a round wooden coffee table with a cheerful brunch spread: mini chicken-and-waffle bites, slider sandwiches, avocado-topped toast, muffins, fresh fruit and assorted savory pastries.

White mobile champagne cart with hanging flutes, rosé and sparkling bottles and a floral arrangement on a sunny backyard patio with a palm tree

Playful mimosa bar setup with two champagne bottles chilling in ice wells, three glass carafes of orange, red, and pale mixers, hot pink balloons and vases, and a gold-framed “Ring for Champagne” sign on a white counter.

Cheerful tiered brunch spread in an indoor entryway — croissants, mini tarts, cupcakes, parfaits, bowls of strawberries and blackberries, citrus halves and assorted pastries arranged on wooden trays with green garlands and crane-pattern wallpaper.

White marble-style champagne cart with large wheel, bright pink and orange balloon garland and floral accents, champagne bottles, colorful carafes and hanging flutes — cheerful indoor party display

Festive event dessert buffet on a white table: tiered cupcakes and mini cakes, trays of donuts and pastries, chocolate-covered strawberries, watermelon wedges, grapes, orange slices and bowls of berries, accented with pink floral arrangements.

White champagne cart decorated with red fabric, gold bows and flowers on an ornate stone terrace at sunset — elegant wedding/event setup

Row of upside-down champagne flutes with red stems hanging from a white rack labeled CHAMPAGNE, surrounded by red glitter hearts and pink balloons — festive Valentine’s Day bar decor

Close-up of a hand holding a heart-shaped glass of pink sparkling drink against a blurred bouquet of pink, white, and red flowers

Vibrant indoor brunch spread on a kitchen island: tiered fruit and dessert stand with grapefruit, grapes, berries and macarons, glasses of orange juice with strawberry garnish, charcuterie, pastries and a large floral centerpiece

Indoor home brunch buffet on a kitchen island with a colorful floral centerpiece, avocado crostini, wraps, pastries, skewers and cheese cubes arranged on platters

Party-ready brunch spread on a granite kitchen island in a bright modern home — large colorful floral centerpiece surrounded by tiered trays of mini sliders, pastries, muffins, skewered appetizers, crostini and green juice shots, with wicker counter chairs.

Colorful brunch spread on a round wooden table: four white plates with mini sliders, waffle bites topped with fried chicken, avocado-topped toast, muffins, quesadillas, chips and fresh berries.

Plan B-runch: Full Brunch Set-Up at Your Location with Mimosa Bar!

3hr

From $65/person

experience

Bridal party in matching floral pajamas popping champagne and toasting by a white champagne cart on a sunny backyard patio — playful bachelorette/bridal shower celebration.

White vintage champagne cart on a columned southern front porch, stocked with hanging wine glasses, pitchers of orange and pink mimosas, buckets of champagne and rosé over ice, floral arrangements and pastries, with oak trees draped in Spanish moss on the lawn.

Brunch-ready outdoor mimosa bar with chilled champagne bottles in ice wells, carafes of orange, cranberry and peach juices, fresh berry platter and a glass bowl of pink macarons on a white table.

Hand placing a pink flower petal as a garnish on a sparkling champagne flute on a bright party table with carafes of red and pale drinks and a chilled bottle in an ice bucket

Sunlit outdoor garden champagne cart under a wooden pergola, styled for a wedding with hanging wine glasses, white floral garlands, pink drapery and ice buckets of champagne.

Sunlit bridal shower mimosa bar on a white table with four glass carafes of colorful juices, two mini champagne bottles in ice wells, a pink floral centerpiece, framed "Ring for Champagne" sign, gold glitter ring cutouts and a "Bride" headband.

White vintage champagne cart with hanging wine glasses, chilled bottles in ice buckets and pink floral arrangements on a sunlit garden brick path for an outdoor event

Sunlit bridal mimosa bar setup with three glass carafes of orange, red, and brown juices, two champagne bottles chilling in ice wells, a bowl of sliced strawberries, a framed bubbly-bar menu and a gold “Bride” headband on a white table.

Sparkly outdoor champagne cart in a sunny backyard, decorated with pink flowers, iridescent bubble ornaments and hanging pink disco balls; glassware overhead, colorful drink carafes and floral arrangements on the cart, ice bucket with champagne bottles by a white fence.

White vintage champagne cart with hanging flutes and three colorful carafes (red, yellow, orange) on artificial turf in a backyard beside a white fence and a "Last Toast" bridal shower banner.

Floral champagne cart in a sunlit woodland garden — white cart draped with pink and purple blooms, hanging champagne flutes, orange juice bottles for mimosas, heart-shaped frame and decorative wheel

White mobile champagne cart with hanging flute glasses, bottles, a yellow juice carafe and white floral arrangements beneath large trees in a sunlit garden, styled for an outdoor event.

Playful champagne bar setup with two chilled sparkling wine bottles in ice wells, three glass carafes of orange, red and pale mixers for mimosas, bright pink balloons and vases, and a gold frame sign reading 'Ring for Champagne'.

White marble champagne cart at an indoor party, decorated with bright pink, orange and confetti balloons, small floral accents, glass carafes of colorful drinks and chilled champagne bottles

Women in matching pink satin robes and sleep masks celebrating in a hallway under iridescent purple streamers, one holding a champagne bottle for a playful bachelorette/girls' night vibe.

Valentine's-themed pop-up champagne and mimosa cart with red heart garlands, red balloons and roses, two chilled champagne bottles and carafes of orange juice on a white marble-style counter

Valentine's-themed indoor champagne cart in a home — white cart with hanging wine glasses, red heart garland, red/black/white balloon column, floral accents and gold ring balloon

Bottomless Mimosa Bar Featuring our Catered Champagne Cart!

3hr

From $55/person

Explore your destination through the lens of someone who’s already been there done that!

experience

Driftwood tree adorned with white seashells on a sunlit tropical beach with shallow turquoise water and a clear blue sky

Silhouetted pontoon boat and person wading at the beach shoreline during a vibrant sunset with a crescent moon over calm ocean waters

Bottle of prosecco on a pontoon boat table at sunset, calm bay waters reflecting city lights with palm trees and waterfront condos in the background.

American flag flying from the stern of a pontoon boat cruising a coastal inlet, wake trailing behind, cushioned seats and table visible under an overcast sky.

Pontoon boat interior with helm and cushioned bench seating at sunset on a calm coastal inlet, pink clouds reflecting on the water and shoreline marina in the distance.

Half Day Island Party at Shell Key

4hr

From $450/party

experience

Sunset view from a pontoon boat: beige cushioned seats and steering console in the foreground, calm water reflecting pink clouds, and a distant shoreline with marina buildings and palm trees.

Small black-and-white dog in a pink harness leaning on the seat of a pontoon boat, smiling toward a pastel sunset over calm coastal waters and marshland.

Aerial view of a lively sandbar boat party with dozens of anchored boats in clear turquoise shallow water and hundreds of people gathered on the sand and swimming.

Pontoon boat interior with beige captain chairs and a round table under a black bimini, facing a calm mangrove-lined canal and docks on a sunny day — ready for a relaxing cruise.

Sparkling golden fireworks over a waterfront marina at night, reflecting on calm harbor water with lit buildings and a boat in the foreground.

Tan pontoon boat with a black bimini canopy docked at a sunny Florida marina, calm water, palm trees and a boardwalk under a bright blue sky with wispy clouds.

Vibrant coastal marina with colorful waterfront shops and restaurants, palm trees along a bustling pier, docked boats and a red tour boat cruising turquoise water.

Sunset silhouette of a red pirate-style tall ship with masts, sails and rigging sailing on calm coastal waters near a tree-lined shore

Silhouetted pontoon boat and two people wading on a calm beach at sunset with a crescent moon above an orange horizon

Playful dolphin swimming at the surface of a turquoise bay with boats and a sunny shoreline in the distance.

Private Custom Boat Charter: Your Dream Day on the Water, IRL

2hr

From $300/party

experience

Bride in white holding a floral bouquet as bridesmaids in satin copper, navy and silver dresses reach hands forward at an outdoor wedding

Smiling group of women in a living room wearing tiaras at a combined bachelorette and birthday party — one in a veil and another wearing a pink "Birthday Girl" sash.

Smiling group of women in white dresses and tiaras celebrating a birthday in a cozy living room; the birthday girl sits front wearing a pink sash and red robe while friends pose with feather boas.

Layered gold and silver chain bracelets cascading over a person's wrist, styled with a flowing rust-red blouse sleeve — close-up fashion accessory shot.

Three smiling people seated at a marble-top table in a cozy nautical-themed lounge, tufted leather banquette and glass-front bookshelves behind them, one holding a large gin-and-tonic with lime.

Bridal party outdoors — bride in a white satin slip dress and three bridesmaids in black showing matching gold bracelets on joined hands

Two Hearts Boutique Permanent Jewelry

1hr 30min

From $45/person, $300/party

experience

Vibrant coastal marina and pier with colorful waterfront shops and palm trees, docks crowded with boats and a small red sightseeing ferry cruising turquoise water on a sunny day

View from a beige pontoon boat helm and wraparound seating toward a calm waterfront at sunset, pink clouds reflecting on the water with a distant shoreline of palm trees and low-rise buildings.

Sunny waterfront open-air restaurant and bar on a lively marina with wooden docks, palm trees and coastal condos in the background

Rustic waterfront pier restaurant on wooden pilings with red awning and outdoor bar seating, diners overlooking emerald-green water and a small boat moored at the dock.

Waterfront dockside outdoor dining deck with blue-topped picnic tables, patio heaters and ceiling fans, blue umbrellas and bridge over the marina

Tiki-style waterfront restaurant on wooden pilings at a marina, warm string lights and open-air seating, illuminated dock and picnic tables reflected in calm water at twilight

Waterfront Bar Hopping on the Intercoastal Waterway

2hr

From $300/party

experience

Evening rooftop yoga and stretch class on artificial turf under string lights on an urban rooftop patio, participants on colorful mats stretching while a DJ/instructor plays music by a glass-front building.

Group yoga class in a tropical-themed studio with a DJ, green mood lighting and participants stretching on mats.

Instructor-led group core workout in a bright fitness studio — participants on mats performing pilates/yoga-style exercises.

Two women in matching black activewear stretch on pink mats during a sunlit outdoor patio yoga class in an urban courtyard with a colorful mural in the background.

Outdoor poolside yoga class on a sunny tropical patio with palm trees and string lights, a group balancing on mats along the pool edge.

Group yoga class in an urban brewery — people on mats doing side-angle stretches beside stainless steel fermentation tanks while a DJ plays music

Group of women in bridge pose on yoga mats in a neon-lit indoor fitness studio with purple-blue lighting

House & Sweat: Fitness & Partying Experiences with Yoga or Pilates + Live DJ

3 Reviews
1hr

From $300/party

experience

Five friends clinking white-wine glasses around a wooden table on a tropical outdoor terrace at sunset with palm trees in the background.

Four women laughing on a rooftop terrace at sunset, toasting glasses of red wine during a casual friends' night

Sommelier pouring red wine into a glass decanter at a wine-tasting table surrounded by bottles and filled wine glasses

Four friends in cozy sweaters toast red wine by floor-to-ceiling windows overlooking a snowy forest — relaxed winter cabin gathering.

Top-down view of four friends in colorful swimsuits sitting on a backyard pool edge, smiling and clinking wine glasses in a summer poolside cheers.

Sommelier-Led Wine Tastings at Your Vacation Rental

1hr 30min

From $100/person

experience

Aerial view of a long, green barrier island with white sandy beaches and a small coastal tower, surrounded by turquoise waters dotted with anchored boats under a sunny blue sky

Champagne bottle spraying over a boat railing as silhouetted partygoers cheer against a sunlit ocean at sunset.

Tan pontoon boat with black bimini top moored at a sunny marina wooden dock over calm water under a vivid blue sky, ready for a leisure cruise.

Aerial view of dozens of boats and pontoons anchored around a packed sandbar party, with crowds of people wading in shallow turquoise coastal water.

View from a pontoon boat helm and cushioned deck looking out over a calm coastal inlet and marina at sunset, pink clouds, waterfront buildings and palm trees reflecting on the water.

Sunlit pontoon boat interior with beige swivel seats and small round table under a black bimini top, docked along a calm mangrove-lined coastal canal with wooden docks and distant waterfront homes.

Island Party at Egmont Key: Drinks Flowing, Crystal-Clear Water + Your Crew Celebrating in Paradise

3 Reviews
8hr

From $800/party

experience

Silhouette of a pontoon boat and a person wading at the shoreline during a vibrant orange-blue coastal sunset with a crescent moon and calm sea reflections.

Bottle of prosecco on a boat table at sunset, waterfront condos and marina lights reflecting on calm bay water

V-shaped boat wake cutting through calm coastal waters toward a vivid orange-pink sunset, a lone seabird skimming the wake with channel markers on the horizon.

Small black-and-white dog in a pink floral harness standing on a pontoon boat seat, leaning on the railing and enjoying a pastel sunset over a calm coastal waterway with mangroves.

Night waterfront fireworks over a marina — sparkling golden bursts above lit condos and boats, colorful shoreline lights reflecting on calm water

Vibrant orange and purple sunset over a calm coastal bay, dramatic clouds and glowing ripples reflecting light on the water with a silhouetted shoreline

Silhouette of a tall-masted pirate-style tour ship with passengers sailing on coastal waters at sunset, orange and purple sky reflecting on rippling sea

Sunset cruise view from a pontoon boat with beige seating and helm in the foreground, calm river reflecting pink clouds and a coastal marina and treeline on the horizon.

Sunset Cruise on the Gulf of Mexico

2hr

From $300/party

experience

Cheerful group of adults posing on a sunny downtown Tampa street beneath a tall vintage green theater marquee and ornate brick facade.

Playful ice-filled glass beverage dispenser with green and yellow rubber ducks, a purple orchid and tropical leaves used as garnish on a wooden table.

Spanish dessert spread with sugar-dusted churro sticks, caramel flan, hot chocolate and coffee, plus grilled crepes with orange slices, set against vibrant red flowers and hand-painted Spanish-style ceramic pitchers.

Happy group of diners at a long table in an upscale downtown restaurant, raising glasses over plates and beers beneath large brass ring chandeliers, cozy leather banquettes and framed art with city street windows at night.

Smiling group of adults posing on a cobblestone downtown Tampa street at dusk beneath a glowing vintage theater marquee and neon sign, with trees and city buildings in the background.

Peach-orange cocktails in stemmed glasses arranged on a yellow tablecloth, each garnished with rosemary sprigs, sugared cranberries and cinnamon sticks for a festive restaurant event.

Vibrant outdoor patio table with ruby-red sangria in stemmed glasses, iced water, plated appetizers (fried bite and salad) and mini dessert cups

Group of nine friends laughing around a rustic wooden table in a cozy bistro-style cafe with wine bottles on shelves, glassware and casual brunch place settings.

Tray of frothy, cinnamon-dusted cappuccinos in white ceramic mugs with spoons, barista-style coffee ready to serve

Hands-on chef in a black jacket and flat cap gesturing behind a marble counter in an open kitchen, two artisan Neapolitan-style pepperoni pizzas on a wooden peel under warm lighting — cozy pizzeria scene.

Frozen yellow pineapple cocktail with lemon and mint in foreground on a wooden table, surrounded by crostini, a colorful charcuterie board and wine glasses at a sunny seaside patio brunch.

Bright charcuterie board on a rustic wooden table at a cafe patio — assorted cheeses (brie), cured meats, cornichons, jams, mustard, nuts, strawberries and raspberries, edible flowers and herbs, with water glasses, a yellow cocktail and a brass table lamp nearby.

Smiling group of people on a riverside promenade at night, standing by a railing with shopping bags, city skyline and a red-lit bridge reflecting in the water under a cloudy sky.

Four adults smiling for a photo under hanging red and green umbrellas on a palm-lined downtown shopping street with storefront displays and festive holiday decor.

Mouthwatering artisan gelato display case with multiple flavored pans — chocolate-drizzled, caramel-swirled and sprinkled varieties with clear scoops in a glass counter.

Outdoor holiday market scene with shoppers gathered around a festive shopfront and vendor table on a pedestrian shopping street, red and green umbrellas suspended overhead, holiday window signs and poinsettias adding seasonal decor.

Women sampling appetizers and pink cocktails at an upscale hotel lounge bar with a marble countertop, pendant lights, wine wall and holiday decor.

Lively evening inside a cozy brick-walled pub: a group gathered at a long table under red neon lights and a vintage chandelier, sharing plates, drinks and conversation.

Group of eight friends smiling around a long white table in a modern restaurant, sharing appetizers, cocktails and plates under warm pendant lights — lively evening dining scene.

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Taste Downtown Tampa Bay: Food, Drinks & Culture

6 Reviews
3hr

From $119/person

experience

Bachelorette boat party: women in matching pink tank tops and sunglasses smiling on a sunny boat, holding canned drinks with a concrete bridge and tropical waterfront in the background.

Friends at a summer lake party on bright inflatable rafts and waist‑deep water, lounging on a large blue float and a pink tube, raising canned drinks and smiling.

Playful bottlenose dolphin leaping from turquoise coastal water beside a boat wake, spray arcing with mangrove-lined shoreline and blue sky in the background.

Group of women in swimsuits relaxing and chatting on a pontoon boat, sun hats and drinks, cruising a sunny coastal bay with docks and sailboats in the background.

Sunlit heart-shaped arrangement of assorted pink, peach and tan seashells neatly laid out on white sandy beach

Three women relaxing under a blue-green beach umbrella on a sandy shore with dune grasses behind, two seated in beach chairs and one kneeling, smiling with a neat row of seashells arranged in the sand

Sun, Sea & Tampa Bay Sandbars! Your Private Party Boat for Up to 16

4hr 30min

From $1,250/party

experience

Four adults seated around a round wooden table in a bright loft-style wellness studio, chatting and sipping while two IV bags on poles hang nearby under a woven pendant light.

Sunlit industrial-style studio with large paned windows — two clinicians set up IV drips behind a round pedestal table while two clients sit nearby

Smiling bald medical professional in black scrubs with a goatee, visible arm tattoos and smartwatch, hands in pockets against a neutral gray studio background — friendly clinical portrait.

Luxury IV Wellness Delivered to You

3 Reviews
30min

From $128/person

experience

IV Glow-Up with Your Girls: Hydrate, Relax & Get Event-Ready image 1

At-home IV therapy: gloved clinician inserting an IV into a seated person's arm on a light-colored living room couch with a large tropical houseplant in the background.

Blonde woman seated at a home dining table receiving a blood draw from a gloved healthcare worker — arm with blue tourniquet and adhesive dressing, syringe, vials, sharps container and hand sanitizer on the table.

Person prepping sterile medical supplies, syringes and vials on a marble dining table in a bright waterfront living room with palm-tree lined balcony and water view

Smiling female healthcare professional in black scrubs and blue gloves holding a syringe, ready for an aesthetic or medical injection against a plain clinic wall

IV Glow-Up with Your Girls: Hydrate, Relax & Get Event-Ready image 8

Relaxed man on a brown leather couch in Clearwater, Florida hooked to an IV drip while eating a sandwich, with a framed mirror, pillows and a 'Superhuman Protocol' text overlay.

Cozy living-room at-home IV therapy session: IV pole with drip bags, clinician administering an infusion at a couch, coffee table strewn with medical supplies and people relaxing.

Group of men at a sunny backyard screened pool party, sitting on a tiled ledge and lounge chairs with lush tropical plants behind; one man in the water raises a drink.

Phlebotomist in blue gloves performing an at-home blood draw on a tattooed man sitting on a brown leather couch wearing a tank top, baseball cap and flip-flops, phone resting on his thigh

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IV Glow-Up with Your Girls: Hydrate, Relax & Get Event-Ready

5 (15)
2hr

From $160/person

experience

Six friends in swimwear smiling on a sailboat deck under a blue sky, enjoying a sunny summer sailing trip on open coastal waters.

Two women in white summer outfits posing barefoot on the bow of a sailboat at a marina, one wearing a straw hat and the other holding a woven tote with a pink waterfront hotel and moored yachts in the background.

Smiling couple cuddling on the bow of a sailboat at sunset, sharing a charcuterie board and bouquet of roses with a distant urban skyline across calm coastal waters

Two sunbathers relaxing on a catamaran trampoline under a white sail, cruising on the deep blue open ocean on a sunny day

White 45-foot catamaran sailboat moored in clear turquoise tropical water under a sunny blue sky with scattered clouds

Romantic barefoot couple in wedding attire embracing on a sailboat bow, holding a floral bouquet above calm coastal waters at golden hour.

Romantic proposal on a sailboat — couple embracing under a white banner that reads 'MARRY ME?' against a clear blue sky

Romantic couple cuddling on the bow of a sailboat, enjoying calm blue ocean and warm golden sunlight

Sailboat deck and cockpit with two gray lounge cushions and a life ring, cruising on calm blue water under a clear sky with a distant coastal skyline.

Cheerful group relaxing on a sailboat at sunset over calm coastal waters, passengers seated on deck and in the cockpit with a champagne bottle nearby and the orange sun low on the horizon.

Sleek white sailboat with blue canvas cover docked in a sunny marina, tall masts and neighboring boats reflected in calm water.

Two women on a sailboat deck at sea, one in a flowing red maxi dress holding a straw tote and the rigging, the other in a patterned mini dress near the mast against a calm, overcast ocean.

Aerial view of a playful pod of dolphins swimming and splashing in clear turquoise ocean water, tails and ripples visible at the surface.

Smiling couple in sunglasses lounging on a sailboat deck, holding a travel tumbler and clasping hands against a sunny ocean backdrop

St. Pete Sailing Charters: Tampa Bay Sailing Tours for Any Occasion

1hr 30min

From $395/party

experience

Smiling shirtless man wearing a red Santa hat and black bow tie in a modern kitchen — festive holiday portrait.

Two smiling women wearing Santa hats and summer dresses, posing outdoors by palm trees with a festive tropical holiday vibe.

Festive holiday photo: smiling woman in a patterned apron stands between two shirtless dancers wearing Santa hats, bow ties and sunglasses, with wrapped gift and pinecone accents.

Smiling woman flanked by two shirtless men wearing Santa hats, sunglasses and bow ties, posing in a festive holiday party scene with a vibrant multicolor paint-splash background.

Large group of friends in swimsuits and summer outfits posing playfully at a colorful indoor party in a modern pink kitchen with geometric painted walls, disco-ball pendant lights and neon ceiling trim.

Joyful holiday portrait of a person in a red Santa hat with dramatic green eyeshadow, bold red lipstick, tree-shaped earrings, a green Christmas scarf and red sequin jacket on a green backdrop.

Shirtless muscular bartender in a black bow tie with a dove chest tattoo posing in front of green bar signage; inset shows him pouring a cocktail behind a stocked bar.

Hire a Sexy Santa for Your Holiday Party in Tampa image 8

Hire a Sexy Santa for Your Holiday Party in Tampa

1hr - 1hr 15min

From $259/party

experience

Happy rider on a red scooter parked on a sandy coastal path beneath palm trees, waving and smiling on a sunny tropical beachside day.

Sun-kissed red scooter parked on a sandy coastal path under palm trees at golden sunset, tropical foliage and a boardwalk in the background.

Cheerful person raising an arm beside a red scooter on a sandy path under a palm tree next to a wooden beach boardwalk and sunny blue sky

Bright red retro scooter parked on sandy beachside under palm trees at golden hour, coastal houses and stop sign in the background.

Red scooter chilling on a sandy beach under palm trees at golden sunset, with footprints in the sand and a wooden boardwalk nearby

Red retro-style scooter with teal accents parked on a sunlit street beside a tree-lined pond and grassy park path.

Three retro-style scooters—yellow, blue, and red—lined up in a bright modern showroom with wood-look flooring, a white display wall of hats and hanging black t-shirts, and a pink neon wall sign.

Red scooter parked in front of a vibrant, multicolored street mural of a serene figure with outstretched arms on a brick wall

Vespa Rental in St. Pete: Feel the Florida Vibes

2hr

From $44/person

experience

Bride in flowing white gown and groom in a light linen suit holding hands as they walk along a sandy beach shoreline at sunset with ocean waves and a faux video REC overlay

Woman in a black jumpsuit and sunglasses walking down a brick‑paved garden path, holding a bouquet of pale pink roses and baby’s breath while smiling and taking a selfie.

Bridal party in a bright dressing suite wearing matching pink satin robes, smiling and holding wrapped sandwiches while getting ready together.

Two women in pink and silver formal gowns sit on a hotel bed while a photographer crouches filming them with a smartphone gimbal in a modern suite

Smiling woman on a sandy beach at sunset filming with a smartphone gimbal, wearing sunglasses, black outfit and white sneakers, coastal condos and palm trees in the background

Close-up of stacked bride and groom hands showing a solitaire diamond engagement ring with a diamond band and a textured gold wedding band, bride’s French-manicured nails and cream suit sleeve visible

Capture Every Moment With Your Personal Content Creator for Unforgettable Group Trips

6hr

From $1,100/party

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